


Tears of Pleasure

by Phayte



Series: Kinktober 2018 [4]
Category: Free!
Genre: Crying, Dacryphilia, Day 4, Kinktober 2018, M/M, Mafia AU, Mirror Sex, One Shot, Plot What Plot/Porn Without Plot
Language: English
Status: Completed
Published: 2018-10-04
Updated: 2018-10-04
Packaged: 2019-07-25 05:00:30
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,600
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16190603
Author URL: https://archiveofourown.org/users/Phayte/pseuds/Phayte
Summary: This is for Day 4 ofKinkTober! Prompt-Mirror Sex | Dacryphilia (Crying)The Prostitute/Mob Boss AU I will never fully write! So a one shot of Rin/Sousuke. Quick backstory to this-- Toono has an agency (prostitutes). Aiichiro rents a boy for the night and works under Sousuke.Sousuke is the head mob boss-- other mobs are after him (of course). Rin is a prostitute from Toono’s agency.





	Tears of Pleasure

**Author's Note:**

  * For [Icicle33 (Icicle)](https://archiveofourown.org/users/Icicle/gifts).



He really needed to give Aiichiro a raise.

“Is this to your liking, sir?” Aiichiro asked.

“You know me almost too well,” he breathed out. Standing over to by the window, was exactly everything Sousuke ever wanted in a man. Not too tall, very lean and muscular... simply beautiful.

“I was able to get him through Toono’s services,” Aiichiro stated.

“Is he showered?” Sousuke asked, unable to take his eyes off the man over by the window who was staring him directly in the eye. It almost made him want to laugh. No one ever stared him in the eye anymore.

Aiichiro jumped with a yelp. “Yes, sir! I had him do that the minute the car pulled up.”

“Good, good. And he is clean?” Sousuke asked. 

“I made sure of it and Toono provided the documents,” Aiichiro said.

“It’s like I am not even here,” the man at the window grumbled, finally looking away from him.

“You’ll speak when told to!” Aiichiro barked. It almost made Sousuke laugh-- for as good as Aiichiro was, he was not aggressive. Though, Sousuke had to give him credit for his efforts.

Walking over to the window, he looked down into the deep burgundy eyes staring back at him. “You must be new,” he stated. When he didn’t answer, he chuckled. “Ok, smartass, you can talk.”

“Not new,” the man mumbled, taking his eyes from him and staring out the window.

“Ah, Aiichiro… you got me a newbie,” he chuckled, brushing the hair from the man’s face, watching the blush spread on his cheeks. Leaning forward, he whispered in the man’s ear, “Don’t worry… I’ll break you in.”

A loud crash and he stood back sighing. Turning and showing his annoyance to Aiichiro-- a sign for him to go see what the hell just happened.

“Sorry sir! I think Momotarou is… loose,” Aiichiro yelped.

“Fuck!” he cried, turning from the man at the window and sitting at his desk. “I told you to have him supervised at all times!”

“I’ll go get him! Sorry, sir!” Aiichiro chirped.

“Ai,” he said, watching as he spun back his way. “You are in charge til morning. Unless the mansion is burning or you are dead, do not bother me.”

Bowing deeply, Aiichiro exclaimed. “Yes, sir!”

The moment the door shut, he turned his sights back to the man at the window. Lifting his hand, he curled his finger, beckoning him to join him at the desk.

“Do you have a name?” he asked.

“Of course I do,” he said, sitting on the edge of his desk, crossing his legs. Sousuke took note how the jeans slug low on his slim hips, and how deep the V was on his shirt-- a pop of cleavage just enough to tease him a bit. Golden bangles on his wrist, and a sparkle to his lips. Yes, this was exactly what Sousuke like.

“May I know it?” he asked, extending his hand, tracing a finger over his knee up his thigh.

“You can call me Rin,” he said, uncrossing his legs, spreading them wide across his desk, trapping Sousuke between them.

“How did Toono get a boy like you in his agency?” Sousuke asked, both hands massaging two very muscular thighs. Fuck, this guy was ripped.

A shrug and Rin smirked at him. “You know the story, college kid… needs money.”

“Oh baby, I can give you money,” Sousuke said, pulling Rin down to his lap.

A toothy grin and Rin wiggled on his lap. “Oh? You going to be my sugar daddy or something?”

Hands moving down his back, cupping his bottom and squeezing. “Definitely something.” Leaning in to kiss, Rin pulled his head back, smirking back down at him. Squinting, Sousuke didn’t like being teased. “I am sure Aiichiro paid for full service.”

A laugh and Rin was leaning against him, his breath hot on his neck-- but not touching. “I am sure he did too… Toono said I am to do whatever you want,” Rin whispered in his ear.

What Sousuke wanted to taste his lips, he didn’t like the way he pulled back. That was the shit hookers did, since hookers didn’t kiss-- and he knew Aiichiro did not go to the corner and pick this guy up-- no, he went through the top agency and got him.

“I don’t like being teased,” he growled, moving his arm to the back of Rin’s head, taking a fistful of hair and pressing their mouths together.

Their mouth moved easily against each other-- Sousuke knew Rin was  _ not _ new at this. Grabbing him harder, he slid Rin further into his lap, cupping his ass and squeezing it hard. Using his tongue to lick over his bottom lip, he sighed the moment Rin’s mouth opened and licked over his teeth then deeper into his mouth. Opening his mouth wider, he wanted to consume this beautiful creature wiggling on his lap.

Hands into that mess of red hair, silky under his fingers-- Rin’s body pressing tightly to his. He was thrilled how tightly toned Rin’s body was. Pulling back from the kiss, he was breathing hard, and he saw Rin’s eyes darkened with lust.

“Bedroom,” he breathed out.

Rin scrambled off his lap, then took his hand. He had a huge mansion, and was not taking him to his personal bedroom-- at least not tonight. Walking down a few dark hallways, he went to the room that Aiichiro said he set up for him.

There was a massive king size canopy bed, mirrors along the side wall and a perfect view of the back orchards. The small lamps on each side of the bed were turned on, putting a soft glow to the room. When Sousuke looked over at Rin, the shadows falling over his face-- he wanted to take him right there.

Letting go of Rin’s hand, he stepped into his personal space, and grabbed the hem of his shirt. Rin lifted his arms, letting the shirt lift off his body. Shaking his hair out, he stared at Sousuke. There was a large studded belt low on Rin’s hips with his jeans. Making quick work, Sousuke had them undone and pushing down his legs.

Stepping back, he smiled to himself. Something this pretty should not be a part of Toono’s crooked ass company.

The way Rin’s hair with a few strands in his face, the way the bangles on his wrist clanked together as he pushed back his hair. The toothy seductive grin he gave Sousuke as he slowly stepped and backed him to the mirrors.

Long thin fingers were unbuttoning his shirt, then hands cold as ice where moving up and down his chest, then down to his waist and back up his sides. It tickled a bit, making him jerk.

“Oh! Ticklish, huh?” Rin asked, stepping even closer so their breath mingled.

“Little bit,” he mumbled, pressing his lips back to Rin’s, moving his hands behind his back right above his ass and pressing his hips into his. He easily felt where Rin was half hard, and his own excitement building. Grabbing at his hips, he spun them so Rin was pressed to the mirrors-- his back against the cold glass. A yelp followed by a gasp-- but Sousuke started to kiss his neck, breathing in the cologne Rin was wearing. It was sweat-- almost like honey.

“You smell amazing,” he said.

“That soap you have in the bathroom.”

“Which bathroom?”

“How big is this place?!” Rin asked.

“The less you know the better,” Sousuke growled into his skin, biting then sucking a dark spot on him.

“Ah! Marks!” Rin exclaimed.

A deep growl, because Sousuke did not care. He knew Toono would never come at him for this-- his boys gave Toono too much business. “I do what I want,” he muttered.

He wanted to touch Rin everywhere and his patience was quickly leaving. Capturing his mouth again, Sousuke kissed him deeply, his tongue gliding over Rin’s as he sucked the air from his lungs.

Hooking his thumbs in the  _ all too small _ panties Rin was wearing, Sousuke tugged at them, removing his mouth from Rin’s to slide them off. The way Rin gasped, his chest heaving from catching his breath only turn him on more. Spinning Rin so he faced the mirror, Sousuke kissed his shoulder, looking at Rin’s face in the mirror as his arms wrapped around him, taking his cock in his hand. Rin gasped and shut his eyes tight.

“Open your eyes,” he growled.

A quick draw of air, and Rin was snapping his eyes open. They were dark and covered in lust-- Sousuke was so close to losing it.

“Fuck…” he groaned. “You are so beautiful.”

“Hah!” 

His hand worked Rin’s cock, all the while, he kept staring at the expressions on Rin’s face. Pressing his hips into Rin’s ass, he kissed the back of his neck, licking up the sides before turning his head, and kissing Rin deeply. Grabbing his shaft harder, Sousuke continued to stroke him, loving how he leaked all into his fist.

“You get so wet,” he mumbled against Rin’s lips, rocking his hips and his now fully hard cock was between his cheeks.  


Rin continued to gasp the more he kissed at his neck and stroked him. When he felt Rin’s cock pulse in his hand, he squeezed the base-- hard. “Do not cum.”

“Hah!” Rin screamed.

“You can be as loud as you want…” Sousuke said with a smirk. He knew in this mansion that two guys were right outside his door-- but he also knew he gave no fucks for anything heard.

Stepping back from Rin, he moved to the dresser, sliding his shirt off his arms then stepping out his pants. Rin was still planted up against the mirror, his body blushed, mouth slightly open as he gasped for air.

“Fuck… that is the…” he couldn’t finish his thought. Seeing Rin already losing himself was perfect-- his pink cock jutting from his hips and seeing Rin in this state pressed against a mirror-- was fucking priceless.

Getting the lube out, he moved back over where Rin was, circling his rim with a wet finger. “You don’t cum til I say so… understand.”  


“Hah!” Rin yelled the moment his thick finger pressed into him. “Yea… I got it.”

It made him chuckle. How long had it been since someone  _ didn’t  _ call him sir? It sort of turned him on more, in a weird way. Pressing his finger harder into Rin, he watched as Rin raised to his toes with each press. The muscles in his legs tensing up-- showing off each heavy line of perfection down his body.

He wanted to mark Rin up, he didn’t want to think after this that Rin would return to Toono’s-- then go to someone else. He would definitely make sure Aiichiro booked this one… and kept him solely for him. 

Leaning forward again, he sucked more marks up and down his shoulders while working another finger in him. Curling his fingers, Rin cried out-- it was choked and mangled sounding.

Staring into the mirror, Rin’s face was twisting and his eyes watering. Looking down his body-- his cock was red and leaking-- he had to be close to cumming.  


“Such a good boy,” Sousuke said, moving a hand to Rin’s straining cock, feeling it heavy and hot in his hand, stroking it once.  


Rin choked out another cry, and tear falling as he did. Red flags were screaming in Sousuke’s mind, though for the moment, his lust was taking him over. He never had a prostitute cry before-- it made his cock even harder.

“Do you cry even more if you don’t cum?” he asked.

Rin nodded, opening his mouth to sob out. “I can’t… I have--”

“--No! Hold it!” he demanded, curling his fingers again, making Rin scream then tears spring from his eyes--he was use to the prostitutes that took forever to cum. “Fuck… I think you are more beautiful when you cry.”

“Not… crying,” Rin sniffled out, choking again when he stroked his cock.

“Maybe I will keep you for the weekend… would you like that?” he asked.

“I’d like to cum!” Rin exclaimed.

“Tell me you’ll stay the weekend then.”

“But I have to check in with Toono.”

“Don’t worry about him, tell me you’ll stay.”

Rin nodded his head and Sousuke kissed his neck-- curling his fingers with one hand, jerking him with the other, Rin sobbed more.

“Oh baby… cum,” he said.

A loud scream and Rin’s body was shaking-- covering the mirror in his release. He felt like he could have cum from the sight alone-- his own cock hard and throbbing. A hand between Rin’s shoulder blades, and he pressed him tighter to the mirror-- his tears smearing the glass. Stroking his cock with lube, he quickly pushed in-- Rin crying out as his body still shook.

He was tight, he was warm-- he was fucking perfection. Sousuke swore his ass was built for his cock and his cock alone. Taking hold of Rin’s hips, he marveled at how slim they were, and how his hands seem to drown them.

He held still-- waiting for Rin’s breathing to ease up a little. He knew his body was in overcharge from the orgasm, but he also knew his balls were aching to release and Rin’s ass was feeling good around his cock.

Sousuke wasn’t stupid… prostitutes didn’t cry unless beaten ( _ not that he beat them _ ). Something was off, but right now all the blood he needed to think was located in his cock.

“I can’t wait anymore,” he groaned, pulling out and slamming back in. Rin crying out, trying to take purchase of the mirror with his hands. Tears streamed down his face the more he pounded into him. Grabbing at Rin’s hair, he tugged him back, smearing the tears down his cheeks and forcing his head to turn to him. Kissing a wet cheek, Sousuke continued to rock his hips in and out of Rin. “You feel fucking perfect.”  


Seeing Rin in the mirror, his mouth open, panting for air, his hair starting to stick to his forehead from sweat, his cock half hard bobbing between his legs-- he was fucking done for. Slamming more in and out of Rin, he never stopped. His orgasm slamming into him, he deeply emptied into Rin’s ass. Holding Rin tightly to his chest, he breathed deeply, trying to calm the racing of his heart. Choking and small sobs, had him look into the mirror, seeing the tears still fall from Rin’s eyes. 

“Baby, are you ok?” he asked, getting a nod in response. Pulling out, he led Rin to the bed, and laid him down. Moving next to him, he cradled him in his arms, kissing his brow. The way Rin held him tightly as his body was still shaking was surprising.

“You aren’t from Toono’s… are you?” he asked.

The arms around him tightened, but he got no answer.

“Look… if I promise to keep you safe,” he said, a hand under Rin’s chin to look at him. “Tell me who sent you.”

A gulp and Rin looked away. Sousuke already knew, but he also knew he could not give Rin up.

“I promise, I won’t harm you.”

“Nanase,” Rin mumbled.

Sousuke already knew before he had said the words. This looked like a boy Nanase would keep around. Maybe an assassin? A hacker? “Are you loyal to him?” he asked.

“Not anymore.”

That was all Sousuke needed to hear. 

**Author's Note:**

> You can find all of upcoming prompts [[HERE](https://phaytesworld.tumblr.com/post/178347715081/kinkytober-which-prompts-are-you-using-cant)]! My goal is to complete ALL of these! I have made these into a collection if you wish to follow them!
> 
> Leave me and comment and Kudos please! That is what keeps me going! You can come chat with me on Tumblr too! I promise I bite!  
> [Phaytesworld ](https://www.tumblr.com/blog/phaytesworld)  
> Phayte <3


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